Toluene → HCID 86739774, compound

HRID 1980205Notes

Reaction equation

HRID 1980205 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1([CH3:19])[C@@H:11]([CH:12]=[C:13]([CH3:15])[CH3:14])[C@@H:10]1[C:16](Cl)=[O:17].[CH3:20][C:21]1([CH3:31])[C@@H:23]([CH:24]=[C:25]([CH3:27])[CH3:26])[C@@H:22]1[C:28]([OH:30])=[O:29]>N1C=CC=CC=1>[CH3:8][C:9]1([CH3:19])[C@@H:11]([CH:12]=[C:13]([CH3:15])[CH3:14])[C@@H:10]1[C:16]([O:30][C:28]([C@H:22]1[C@H:23]([CH:24]=[C:25]([CH3:27])[CH3:26])[C:21]1([CH3:31])[CH3:20])=[O:29])=[O:17]

Participants

5

Reactant 3

HCID 1140TolueneHCID 33607(1S-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acidHCID 54401499(1S,3S)-2,2-Dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarbonyl chloride

Product 1

HCID 86739774HCID 86739774, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 500 ml flask were placed 200 g of toluene, 27.8 g of (-)-trans-2,2-dimethyl-3-isobutenylcyclopropane-1-carboxylic acid chloride and 25.0 g of (-)-trans-2,2-dimethyl-3-isobutenylcyclopropane-1-carboxylic acid. Into the mixture was added drop-wise 11.9 g pyridine, while stirring under nitrogen at a temperature of 20° to 25° C. After 5 hours, the reaction mixture was washed sequentially with an aqueous 10% hydrogen chloride solution, an aqueous 5% sodium hydroxide solution, and water, and then concentrated in vacuo. The residue was distilled in vacuo at boiling point 130° to 135° C./0.2 mmHg, to obtain 46.1 g of (-)-trans-2,2-dimethyl-3-isobutenylcyclopropane-1-carboxylic acid anhydride, with [α]D -17.3° (C=1, CH2Cl2).

Workup

  1. customIn a 500 ml flask were placed
  2. washthe reaction mixture was washed sequentially with an aqueous 10% hydrogen chloride solution
  3. concentrationan aqueous 5% sodium hydroxide solution, and water, and then concentrated in vacuo
  4. distillationThe residue was distilled in vacuo at boiling point 130° to 135° C./0.2 mmHg

Sources & evidence

ORD record
ord-940258c6146a4f0eb6ef31832c04f1c6
Source dataset
uspto-grants-1984_11
Patent number
US04485257

Reaction notes

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